94533-57-0Relevant articles and documents
Reductive coupling of aromatic N,N-acetals using zinc and chlorotrimethylsilane
Hatano, Bunpei,Tachikawa, Tomoharu,Mori, Tetsunori,Nagahashi, Keita,Kijima, Tatsuro
supporting information; experimental part, p. 3467 - 3469 (2011/07/08)
The reductive coupling of aromatic N,N-acetals and N,O-acetal activated by chlorotrimethylsilane proceeded smoothly in the presence of zinc to give the corresponding diamines in good yields.
An efficient method for the preparation of vicinal tertiary diamines by reductive coupling of aminoacetals mediated by low valent titanium iodide species
Yoshimura, Naritoshi,Mukaiyama, Teruaki
, p. 1334 - 1335 (2007/10/03)
Aminoacetals, easily prepared by condensation of aromatic aldehydes, secondary amines and alcohols, are reductively coupled by using low valent titanium iodide species to afford the corresponding coupling products, vicinal tertiary diamines, in good to hi
Photochemistry of Intramolecular Charge Transfer Excited States in Donor-Acceptor-Substituted Diamines
Wang, Yingsheng,Schanze, Kirk S.
, p. 6876 - 6888 (2007/10/02)
The photochemistry and photophysics of 1,2-diamines C5H10NCHPhCHPhNHC6H4R (1, R=CN, and 2, R=4-pyridyl) have been examined.These compounds display a strong absorption band in the near-UV which is due to intramolecular charge transfer from the secondary amine group to the 4-cyanophenyl or (4-pyridyl)phenyl acceptor unit.Photoexcitation into this absorption band leads to moderately intense fluorescence from the 1LE state of the charge transfer chromophore and to homolytic bond fragmentation across the 1,2 C-C bond with moderate quantum efficiency.Detailed photochemical and photophysical studies reveal that the bond fragmentation reaction ensues from a second intramolecular charge transfer excited state (denoted 1CT) which is based on electron transfer from the tertiary piperidine nitrogen to the 4-cyanophenyl or (4-pyridyl)phenyl unit.Photochemical product analysis reveals that erythro -> threo (or threo -> erythro) isomerization occurs under both argon-degassed and air-saturated conditions.This observation indicates that recombination of the radicals formed by bond fragmentation occurs, both within the geminate pair and between free radicals that have escaped the solvent cage.Analysis of fluorescence, transient absorption, and steady-state photochemical kinetics data indicates that (1) internal conversion from the 1LE state to the 1CT state by intramolecular electron transfer occurs with k>/=109 s-1 in all of the diamines; (2) bond fragmentation within the 1CT state occurs with k>/=108 s-1 in each of the diamines; (3) bond fragmentation may be faster in erythro-1 than in threo-1.
Aminierende, reduktive Kupplung aromatischer Aldehyde mit Tris(dialkylamino)methylvanadium(IV) zu N,N,N',N'-Tetraalkyl-1,2-diarylaethylendiaminen
Imwinkelried, Rene,Seebach, Dieter
, p. 1496 - 1502 (2007/10/02)
In a novel type of reaction, certain aromatic aldehydes (benzaldehyde, p-methoxy-benzaldehyde, 1-naphthaldehyde, furan-2-carbaldehyde) and secondary amines are coupled to give N,N,N',N'-tetraalkyl-1,2-diarylethylenediamines 1-6.The reagents are tris(dialkylamino)methylvanadium(IV) compounds (cf.Eqn.2).These are generated in situ either from isolable chlorotris(dialkylamino)vanadium(IV) (Eqn. 3), or preferably, from an Et2O/pentane solution of VCl4 which is treated sequentially with 3 equiv. of lithium dialkylamide, 1 equiv. of MeLi, and equiv. of aromatic aldehyde, to give the products 1-6 in a one-pot preparation (Schem 2).The yields range from 14 to 54percent.The diastereomeric mixtures (meso- and (+/-)forms) obtained are separated by chromatography (Al2O3, petroleum ether/Et2O/Et3N), and the pure stereoisomers fully characterized.A mechanism of the reductive coupling induced by CH3V(NR2)3 is proposed (Scheme 1).
